The present invention relates to a low-irritant pesticidal emulsifiable concentrate which can be used as an emulsion which is superior in emulsion stability when using after diluting with water.
A pesticidal active ingredient compound is normally used in various forms which are easy to use, and one of a normal preparation for pyriproxyfen and a pyrethroid compound is an emulsifiable concentrate.
The pesticidal emulsifiable concentrate is normally composed of a pesticidal active ingredient compound, a surfactant and an organic solvent, and is used after diluting with water. Various trials are made in selection of surfactants, selection of organic solvents and their combinations on making the pesticidal emulsifiable concentrate in order to enhance the emulsion stability of emulsion obtained by diluting with water and to reduce toxicity, phytotoxicity to crops, etc. depending on the kind of the pesticidal active ingredient compound,.
An object of the present invention is to provide a pesticidal emulsifiable concentrate which is superior in emulsion stability on dilution with water and low irritant.
The present invention provides a pesticidal emulsifiable concentrate comprising (a) 1 to 60% by weight of at least one pesticidal active ingredient compound selected from the group consisting of pyriproxyfen and a pyrethroid compound, (b) 2 to 15% by weight of at least one surfactant and (c) 15 to 90% by weight of at least one aromatic ester solvent represented by the formula:
Arxe2x80x94Xxe2x80x94COORxe2x80x83xe2x80x83[1]
or the formula:
RCOOxe2x80x94Xxe2x80x94Arxe2x80x83xe2x80x83[2]
[wherein R represents non-aromatic group having 1 to 6 carbon atoms; Ar represents an aromatic group; and X represents a single bond or an alkylene group having 1 to 6 carbon atoms] which is superior in emulsion stability on dilution with water and low irritant.
In the pesticidal active ingredient compound used in the present invention, examples of the pyrethroid compound includes compounds represented by the formula: 
[Wherein R1 represents a group of the formula: 
[wherein Y1 and Y2 are the same or different and each represents a methyl group, a trifluoromethyl group, a halogen atom or an alkoxycarbonyl group (the number of carbon atoms of the alkoxy group is from 1 to 4); and Z represents a halogen atom or a difluoromethoxy group]; R2 represents a hydrogen atom or a cyano group; and R3 represents a hydrogen atom or a fluorine atom].
Examples of the compounds represented by the formula [3] include pyrethroid compounds such as Fenvalerate [xcex1-cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutyrate], es-Fenvalerate [(S)-xcex1-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate], Fenpropathrin [xcex1-cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate], Permethrin [3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], Cypermethrin [xcex1-cyano-3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], d-phenothrin [3-phenoxybenzyl (1R)-chrysanthemate], Cyphenothrin [xcex1-cyano-3-phenoxybenzyl (1R)-chrysanthemate], Cyhalothrin [xcex1-cyano-3-phenoxybenzyl (Z)-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate], Cyfluthrin [xcex1-cyano-4-fluoro-3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], Flucythrinate [xcex1-cyano-3-phenoxybenzyl (S)-2-(4-difluoromethoxyphenyl)-3-methylbutyrate], etc.
It is also possible used pyrethroid compounds such as Tralomethrin [(S)-xcex1-cyano-3-phenoxybenzyl 2,2-dimethyl-3-(1,2,2,2-tetrabromoethyl)cyclopropanecarboxylate], Allethrin [3-allyl-2-methyl-4-oxo-2-cyclopentenyl-chrysanthemate], Cycloprothrin [xcex1-cyano-3-phenoxybenzyl 2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylate], Fluvalinate [xcex1-cyano-3-phenoxybenzyl N-(2-chloro-xcex1, xcex1, xcex1-trifluoro-p-tolyl)valinate], Etofenprox [2-(4-ethoxyphenyl)-2-methylpropyl 3-phenoxybenzyl ether], etc. as the pesticidal active ingredient compound in the pesticidal emulsifiable concentrate of the present invention.
The pesticidal active ingredient compound is contained in the pesticidal emulsifiable concentrate of the present invention in an amount of 1 to 60% by weight, preferably 2 to 40% by weight.
Examples of the surfactant used in the present invention include nonionic surfactants such as polyoxyethylene polyoxypropylene block polymer, fatty acid ester of polyoxyethylene polyoxypropylene block polymer, polyoxyethylene polyoxypropylene polyaryl ether, polyoxyethylene polyoxypropylene alkyl aryl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene vegetable oil (e.g. polyoxyethylene castor oil), polyoxyethylene polyaryl ether, polyoxyethylene polyaryl ether polymer, polyoxyethylene hardened vegetable oil (e.g. polyoxyethylene hardened castor oil), polyoxyethylene fatty acid ester, polyoxyethylene alkyl ether, polyoxyethylene tristyryl phenylphosphate diester, polyoxyethylene polyoxypropylenetristyryl phenylphosphate diester, fatty acid alcohol polyglycol ether, glycerin fatty acid ester, etc.; and anionic surfactants such as alkaline earth metal salt (e.g. calcium salt) and amine salt of alkyl aryl phosphate, alkali earth metal salt (e.g. calcium salt) and amine salt of alkylaryl sulfonate, alkaline earth metal salt of polyoxyethylene alkyl aryl sulfonate, alkaline earth metal salt (e.g. calcium salt) of polyoxyethylene alkyl aryl phosphate, alkaline earth metal salt (e.g. calcium salt) of polyoxyethylene polyaryl phosphate, alkaline earth metal salt (e.g. calcium salt) and amine salt of dialkylsulfosuccinate, etc. Among them, polyoxyethylene polyaryl ether (e.g. polyoxyethylene tristyryl phenol ether), polyoxyethylene polyoxypropylene polyaryl ether (e.g. polyoxyethylene polyoxypropylene tristyrylphenol ether), polyoxyethylene castor oil, polyoxyethylene hardened castor oil, and salt of alkyl aryl sulfonate (e.g. calcium dodecylbenzene sulfonate) are preferred. The surfactant is contained in the pesticidal emulsifiable concentrate of the present invention in an amount of 2 to 15% by weight, preferably 2 to 10% by weight.
In the aromatic ester solvent used in the present invention, Ar of formula [1] and formula [2] is preferably a phenyl group which may be substituted with at least one methyl group, etc.; X is preferably a single bond, a methylene group or an ethylene group; R is preferably an alkyl group having 1 to 6 carbon atoms.
Preferable examples of the aromatic ester solvent include benzyl esters such as benzyl acetate, etc.; phenyl esters such as phenyl acetate, etc.; tolyl esters such as p-tolyl acetate, etc.; 4-phenylbutyl esters such as 4-phenylbutyl acetate, etc.; benzoate esters such as methyl benzoate, ethyl benzoate, propyl benzoate, butyl benzoate, isoamyl benzoate, etc.; methyl benzoates such as ethyl 2-methyl bezoate, methyl 2-methylbenzoate, ethyl 3-methylbenzoate, ethyl 4-methylbenzoate, etc., phenyl propionates such as ethyl phenyl propionate, etc., phenyl acetates such as ethyl phenylacetate, etc.
The aromatic ester solvent is contained in the pesticidal emulsifiable concentrate of the present invention in an amount of 15 to 90% by weight, preferably 20 to 60% by weight.
The pesticidal emulsifiable concentrate of the present invention may further contain other solvents, additives, etc., in addition to the pesticidal active ingredient compound (a), the surfactant (b), and the aromatic ester solvent (c), if necessary.
Examples of the solvent include aromatic hydrocarbon solvents such as alkylbenzenes (ex. xylene, tetramethylbenzene, etc.), alkylnaphthalenes (ex. methylnaphthalene, etc.), diphenylethane, dixylylethane, phenylxylylethane, etc.; non-aromatic ester solvents such as methyl laurate, isopropyl myristate, isopropyl palmitate, methyl caprinate, methyl oleate, isobutyl oleate, butyl propionate, isoamyl propionate, ethyl butyrate, butyl butyrate, isoamyl butyrate, isoamyl isovalerate, amyl lactate, methyl linoleate, methyl linolenate, coconut fatty acid methyl, etc.; vegetable oils such as soybean oil, corn oil, rape seed oil, linseed oil, castor oil, cottonseed oil, peanut oil, sesame oil, etc.; aliphatic hydrocarbon solvents; alcohol solvents such as 2-ethyl hexanol, etc.; and ketone solvents such as cyclohexanone, acetophenone, etc.
Examples of the additives include antioxidants such as 3-/2-t-butyl-4-hydroxyanisole, butylatedhydroxytoluene, etc.; and pigments.
The pesticidal emulsifiable concentrate of the present invention are normally used as an agent for foliar treatment, or seed treatment.
When using in the foliar treatment, an emulsion prepared by diluting the pesticidal emulsifiable concentrate of the present invention with water (generally from about 100 to 5000 times) is normally applied to foliage, although the concentration varies depending on the kind and content of the active ingredient. Also, an emulsion prepared by diluting the pesticidal emulsifiable concentrate of the present invention with water (generally from about 10 to 5000 times) may be aerial-applied by a helicopter.
When using in the seed treatment, seeds are dipped in a dilution of the pesticidal emulsifiable concentrate of the present invention prepared by diluting with water (from about 10 to 100 times), or a dilution of the pesticidal emulsifiable concentrate of the present invention prepared by diluting with water (from about 2 to 100 times) is sprayed to seed.